Cross dressing, how to tell her?

September 15, 2023

OK, so I've been with this woman just over 4 years now. We're getting married next year and she's moving in with me in about a month.

She knows I'm bi but she doesn't know I've been cross dressing since childhood. For me it's about the sensation of the materials that lingerie is made of and is purely a sexual turn on thing, not that I want to be a woman etc.

I feel that I need to tell her about this but she's quite vanilla and doesn't know the extent of my kinky side (I have other fetishes too).

How can I broach the subject without scaring her off? Have you found yourself in a similar position, on either side, having a man who cross dresses or being a cross dresser yourself?

Thanks!

September 15, 2023

This is something you need to bring up before getting married. Try working it into your intimacy. Joking out her panties on one and mention how comfy they are.

Regardless of how you do it it needs to be done before you get married.

September 15, 2023

I’ve never been in that type of situation but it’s so important for your partner to understand that side of you. Just sit her down and tell her - If she’s uncomfortable, that’s fair. But if she downright can’t accept it then that’s not the person for you.

September 15, 2023

I would say not telling her will scar her. As they will find out eventually find out.

Also, if you tell them and do not accept you. Then I dare say that you would not be yourself.

How to bring up the subject go to drag bingo or start watching world movies I suggest kinky boots and or ***less.

I would say just as long as you are open an honest about how you feel with them. They should accept it.

If not. They are an a**ehole.

My father liked dressing up. He did not tell mum. Causing a shock.

I commented as I think everyone should be themselves in a relationship. I dated a woman for 7 years. I changed many parts of myself that eventually caused damage. Which is the reason for my comment.

Do not change or try to hide major parts of who you are. If they do not accept you. You are worth better.

September 15, 2023

I wish you would have brought this up 4 years ago so that if it isn't something she can't accept then neither party would have time wasted. You have to prepare yourself for literally any reaction. I personally think this a multiple time conversation unless she accepts it without any questions but she may have questions later.

September 15, 2023

I’ve found that just opening yourself up to your more feminine and kinky feelings and being more genuine around her is actually really good. Most women, regardless of sexual preference or experience, appreciate someone who can open up more and be in touch with themselves and who they are. Just explaining it exactly how you told us, where you sometimes enjoy the feeling of lingerie on your body and wearing it feels sexy to you, can be a really fun and simple way to introduce her to your spicy side in a comfortable and relaxed way

September 15, 2023

Way to much after the fact and quite frankly, emotionally hostile and manipulative to not have been upfront in early days, my guy. On track for unhappy days IMHO. Is she reveals she secretly loves it and or just accepts that about you, you’re getting off easy IMHO and still I say tsk tsk tsk.

September 15, 2023

If I were her I would be more upset about the lack of honesty. Having a kink is totally acceptable, not being open and honest about your vulnerabilities is a much bigger issue. You need to tell the truth as soon as possible.

September 15, 2023

I'd also tell her you know you can talk to her about anything but you're still nervous and express that you'll answer all of her questions

September 15, 2023

A misunderstanding for so many ppl. Men want to feel sexy and wanted too. It's just a lot harder.. especially in this society.. so.. be honest. And maybe you two can find a way to make you feel sexy together.

September 15, 2023

Imma be real for a moment cuz everyone seems to have the advice part down.

Why are you marrying someone who doesnt know who you are in full? This feels like it should be a pre-engagement discussion

September 15, 2023

coming out as any identity is hard and scary and this person means a lot to you. i think the most important things are - prepare a bit, doesn't have to be exactly what you're gonna say just what things you want to cover maybe (crossdress, its a sexual thing not a trans thing, you wanted them to know for transparency, +anything else maybe mentioning youve done this since a kid) and then the other really important thing is finding a time when both your partner and you are in relatively calm moods because if someone was already in a bad mood they could say a bunch of hurtful things they later don't actually mean. also ive done smth like "do you have time later today" "at 3 ok cool" and then doing the "i have something to tell you" right before saying what it is that way there's not too much time in the "oh no what is he going to tell me" thought. sorry that was long this is just my advice as a trans dude who has had to come out to a lot of people. good luck! :)

September 15, 2023

Thats a very risky move. Since you known each other a long time it is best to tell her before you get married. As she going to find out sooner or later. Iv not been in this situation and always upfront with my kink. Maybe ask her what her view is on the kink and then open up from there.

September 15, 2023

1 hour ago, wolf17 said:

Thats a very risky move. Since you known each other a long time it is best to tell her before you get married. As she going to find out sooner or later. Iv not been in this situation and always upfront with my kink. Maybe ask her what her view is on the kink and then open up from there.
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I think that would be good advice were this early stages, y otherwise that opens up the possibility for him to keep it secret if she rejects it. 🤷🏻‍♀️

September 15, 2023

Way too far down the line to be telling her, BUT it is what it is and you absolutely have to sit her down and tell her BEFORE you get married or being honest BEFORE too much longer.
.
You also have to be prepared for her to walk away, not because you like to wear (though she may do so because it's not for her) but BECAUSE you have effectively been dishonest for the four years you've been together.
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Also there's no way to sugar coat it, you just need to be open and honest with her, tell her exactly what you do and why you enjoy it and let her decide for herself whether she can accept the deception and the dressing.

September 15, 2023

Good morning danonwheels.

I agree with @gemini_man100% on this one. You do have to be completely honest with her - and before she moves in … never mind before you tie the knot. I don’t cross dress myself, but I do have a very good friend - who managed to keep it a secret from his wife, for about 20 years …
Until she accidentally caught him - fully dressed, in her clothes. She didn’t take it well, and now they have gone their separate ways. You mention that she is quite vanilla, but also that she knows you are bi.
That might be your starting point -right there. Is she fully accepting of your bisexuality?
Do you have an understanding in place regarding this?
How did she find this out? - did you tell her ?
Her reaction to that might give you some understanding as to how open minded she actually is going to be.
You mention ‘other fetishes’ in your post…
Do you consider cross dressing to be the pinnacle of these ? - is there something else that you are into, which you could bring up in conversation, which might give you some indication of how accepting she might be of any of your kinks - without the risk of her walking away ?.
When my ex wife and I were still dating, I wanted to be completely honest with her about my kinks. She knew about my primary ones, namely big breast sex and spanking - and she was happy to indulge me in those.. however one day we ended up at a party, and another couple were VERY flirty with both of us. I recognised that we had an opportunity for a group sex session pretty much straight away… however she didn’t get the vibe at all.
The following day, we were talking, and I mentioned the previous evening - and their behaviour towards us.
Her response …” ewww, that’s disgusting. You’re not one of those “swingers”- are you??!”
Needless to say, that subject was never broached again during our marriage.
We actually lasted eight years, but I had to curb my various kinks for that time, and it didn’t go well.
When you do tell her, she may be confused, upset… there will be a range of emotions, so be prepared for this - as much as possible.
The flip side is this - she may already know - or suspect !
We are not always as clever - or cautious, as we think we are.
Be prepared for this also.

I would say this - DON’T tell her by showing her !…. (I know of someone who did do this.) She probably won’t react well to coming round and finding you fully dressed… even though that may seem like the easy option !
I wish you good luck, and hope all works out well for you both.

September 15, 2023

If she loves you and your honest, then you should be A Ok

September 15, 2023

I recently told my partner the extent of my kinks after about 5 years and what was helpful was explaining at the beginning of the conversation why it was so hard to open up and my by I was nervous to tell her. It was hard but I asked her to hear me out with an open mind and that my *** was being judged and she took it much better than if I had not shared my ***s about being open. Explain to her WHY it has taken so long and why her opinion matters so much to you. Good luck 🫶

September 15, 2023

You absolutely need to tell her, and other commenters are right, before she moves in for sure.

I would keep it very simple, as you have done here - say “hey x, I love you and want to tell you about something that’s important to me, that I didn’t feel confident about telling you before. But I want to be honest with you in everything because we are going to share a life together.” Then say exactly what you have here: that it’s not sexual, that it’s something you really enjoy and is a turn on, but not something you need her to be involved with if she doesn’t want to.

Be prepared for the fact she may feel hurt that you’ve kept this a secret for so long; our feelings are irrational after all! Also be prepared for the fact she may not want to be involved with your kink at all, given she is vanilla.

her first reaction may be positive or not, but if it doesn’t go well then she might just need some time to think/process. Offer reassurance if you can that you liking this, and choosing not to tell her before, is nothing to do with her and down to you. It is common for people to feel insecure (which can manifest as anger or upset) about something like this seemingly “coming out of nowhere” from their perspective.

I hope the conversation goes well and you continue to be very happy together.

September 15, 2023

1 minute ago, ladyomalley said:

You absolutely need to tell her, and other commenters are right, before she moves in for sure.

I would keep it very simple, as you have done here - say “hey x, I love you and want to tell you about something that’s important to me, that I didn’t feel confident about telling you before. But I want to be honest with you in everything because we are going to share a life together.” Then say exactly what you have here: that it’s not sexual, that it’s something you really enjoy and is a turn on, but not something you need her to be involved with if she doesn’t want to.

Be prepared for the fact she may feel hurt that you’ve kept this a secret for so long; our feelings are irrational after all! Also be prepared for the fact she may not want to be involved with your kink at all, given she is vanilla.

her first reaction may be positive or not, but if it doesn’t go well then she might just need some time to think/process. Offer reassurance if you can that you liking this, and choosing not to tell her before, is nothing to do with her and down to you. It is common for people to feel insecure (which can manifest as anger or upset) about something like this seemingly “coming out of nowhere” from their perspective.

I hope the conversation goes well and you continue to be very happy together.
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I meant “not a sexuality issue” in my previous comment.

September 15, 2023

there isn't really an easy way - but certainly before you move in together it is important to find a way, find a time, find a moment to raise it.

September 15, 2023

Thank you all for the replies and advice. Plenty of food for thought. X

September 16, 2023

everyone here commenting is already BIASED. you had 4 years to tell.her...I say you're likely f**ked. You can use many ways to gauge her feelings towards this kink but if she rejects it...you are doomed...you will either have to commit to some type of therapy or leave her. If you are very lucky she won't give a f**k and enjoy it...doubtful as you have omitted this intimate side of yourself.

September 16, 2023

It definitely seems like a bit of a goof not to have mentioned something about this intimate a part of you in four years of you knowing each other, but that’s why it should be an open conversation sooner than later. Especially in marriage, you should accept each other as fully as you would the other. If she couldn’t accept this part of you before you married, she definitely won’t once you are. Sit down and have an open conversation with her and explain it. If you want to keep doing it, she should be aware of and accepting of it the same as any other part of you. Sorry it took you so long to finally have that talk. Hope it goes well.